Potassium Carbonate → 5,6-Dichloro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]sulfinyl]benzimidazole

HRID 1709773Notes

Reaction equation

HRID 1709773 reaction equation
[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[N:6]=[C:7]([S:9][CH2:10][C:11]3[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][N:12]=3)[NH:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-:24].[K+].[K+].ClC1C=CC=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO.O>[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[N:6]=[C:7]([S:9]([CH2:10][C:11]3[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][N:12]=3)=[O:24])[NH:8][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 230365205,6-Dichloro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]benzimidazole

Product 1

HCID 230365365,6-Dichloro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]sulfinyl]benzimidazole

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g of 5,6-dichloro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]benzimidazole in 150 ml of methylene chloride and 30 ml of methanol was treated with 0.5 g of potassium carbonate. 0.6 g of m-chloroperbenzoic acid was added thereto at -30° while stirring, whereupon the solution was stirred for an additional 5 minutes and subsequently poured into a mixture of 20 ml of saturated sodium bicarbonate solution and 20 ml of water. The separated organic phase was dried over sodium sulfate, treated with 0.5 ml of triethylamine and evaporated in a vacuum. Crystallization from methylene chloride-methanol-ether yielded 5,6-dichloro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]sulfinyl]benzimidazole of melting point 173°.

Workup

  1. stirringwas stirred for an additional 5 minutes
  2. dry with materialThe separated organic phase was dried over sodium sulfate
  3. additiontreated with 0.5 ml of triethylamine
  4. customevaporated in a vacuum
  5. customCrystallization from methylene chloride-methanol-ether

Sources & evidence

ORD record
ord-e8c259b9dbb245c09a1e2047bfd7d12b
Source dataset
uspto-grants-1990_08
Patent number
US04950677

Reaction notes

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